EP4240342B1 - Substituierte resorcylsäure-verbindungen als ampk-aktivator und deren verwendung - Google Patents

Substituierte resorcylsäure-verbindungen als ampk-aktivator und deren verwendung

Info

Publication number
EP4240342B1
EP4240342B1 EP21798399.8A EP21798399A EP4240342B1 EP 4240342 B1 EP4240342 B1 EP 4240342B1 EP 21798399 A EP21798399 A EP 21798399A EP 4240342 B1 EP4240342 B1 EP 4240342B1
Authority
EP
European Patent Office
Prior art keywords
compound
ampk
methyl
alkyl
chain
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
EP21798399.8A
Other languages
English (en)
French (fr)
Other versions
EP4240342A1 (de
Inventor
Denis Marcel Barron
Olivier CICLET
Martine NARANJO PINTA
Katyayanee NEOPANE
Yann RATINAUD
Matthew Sanders
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Societe des Produits Nestle SA
Nestle SA
Original Assignee
Societe des Produits Nestle SA
Nestle SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Societe des Produits Nestle SA, Nestle SA filed Critical Societe des Produits Nestle SA
Publication of EP4240342A1 publication Critical patent/EP4240342A1/de
Application granted granted Critical
Publication of EP4240342B1 publication Critical patent/EP4240342B1/de
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/658—Medicinal preparations containing organic active ingredients o-phenolic cannabinoids, e.g. cannabidiol, cannabigerolic acid, cannabichromene or tetrahydrocannabinol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics

Landscapes

  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Epidemiology (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Non-Alcoholic Beverages (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Claims (9)

  1. Verbindung zur Verwendung bei einer Behandlung oder Vorbeugung einer nicht-alkoholischen Fettlebererkrankung bei einem Subjekt, die die allgemeinen Formel I aufweist: wobei:
    R1 aus OH oder O-Glycosid ausgewählt ist;
    R2 aus [3-Methyl-3-(4-methyl-3-penten-1-yl)-2-oxiranyl]methyl (Geranyl-2,3-epoxid) (2e); 3-Methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl (2g); (2E)-3,7-Dimethyl-2,6-octadien-1-yl (Geranyl) (2h); (2Z)-3,7-Dimethyl-2,6-octadien-1-yl (Neryl) (2i); oder 5-Methyl-2-(1-methylethyl)cyclohexyl (2o) ausgewählt ist;
    R3 aus OH, OCH3 oder O-Glycosid ausgewählt ist;
    R4 H ist;
    R5 aus CH3; n-Propyl, n-Butyl oder Pentyl ausgewählt ist.
  2. Verbindung zur Verwendung nach Anspruch 1, wobei die Verbindung der allgemeinen Formel I Cannabidiolsäure, CAS-Nummer 1244-58-2, ist.
  3. Verbindung zur Verwendung nach Anspruch 1 oder 2, wobei die Verbindung aus einer Pflanze oder einem Pflanzenextrakt gewonnen wird.
  4. Zusammensetzung zur Verwendung bei der Behandlung oder Vorbeugung einer nicht-alkoholischen Fettlebererkrankung bei einem Subjekt, die Zusammensetzung umfassend eine Verbindung der allgemeinen Formel I, wie in einem der Ansprüche 1 bis 3 definiert.
  5. Zusammensetzung zur Verwendung nach Anspruch 4, wobei die Zusammensetzung ein Lebensmittel, ein Getränk oder ein Nahrungsergänzungsmittel ist.
  6. Zusammensetzung zur Verwendung nach Anspruch 4, wobei die Zusammensetzung ferner einen pharmazeutisch verträglichen Träger umfasst.
  7. Zusammensetzung zur Verwendung nach einem der Ansprüche 4 bis 6, wobei die Verbindung der allgemeinen Formel I die Verbindung 1; Cannabidiolsäure, CAS-Nummer 1244-58-2, ist.
  8. Pharmazeutische Zusammensetzung zur Verwendung bei der Behandlung oder Vorbeugung einer nicht-alkoholischen Fettlebererkrankung bei einem Subjekt, umfassend eine therapeutisch wirksame Menge einer Verbindung der allgemeinen Formel I wie in einem der Ansprüche 1 bis 3 definiert, oder ein pharmazeutisch verträgliches Salz oder Solvat davon, als Wirkstoff, und einen pharmazeutisch verträglichen Träger.
  9. In-vitro-Verfahren zum Aktivieren von AMPK, umfassend ein Berühren einer Verbindung der allgemeinen Formel I nach einem der Ansprüche 1 bis 3 mit AMPK.
EP21798399.8A 2020-11-05 2021-11-02 Substituierte resorcylsäure-verbindungen als ampk-aktivator und deren verwendung Active EP4240342B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP20205952 2020-11-05
PCT/EP2021/080298 WO2022096423A1 (en) 2020-11-05 2021-11-02 Substituted resorcylic acid compounds as ampk activator and uses thereof

Related Child Applications (1)

Application Number Title Priority Date Filing Date
EP26165504.7 Division-Into 2026-03-17

Publications (2)

Publication Number Publication Date
EP4240342A1 EP4240342A1 (de) 2023-09-13
EP4240342B1 true EP4240342B1 (de) 2026-04-29

Family

ID=73138716

Family Applications (1)

Application Number Title Priority Date Filing Date
EP21798399.8A Active EP4240342B1 (de) 2020-11-05 2021-11-02 Substituierte resorcylsäure-verbindungen als ampk-aktivator und deren verwendung

Country Status (7)

Country Link
US (1) US20230414638A1 (de)
EP (1) EP4240342B1 (de)
JP (1) JP7833458B2 (de)
CN (1) CN116761791A (de)
AU (1) AU2021375455A1 (de)
CA (1) CA3192827A1 (de)
WO (1) WO2022096423A1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4518847A1 (de) * 2022-05-04 2025-03-12 Société des Produits Nestlé S.A. Ampk-aktivator (cbda) und sglt2-inhibitor für metabolische gesundheit

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021245672A1 (en) * 2020-06-03 2021-12-09 Epm (Ip), Inc. Cannabigerolic acid (cbga) derivatives and uses thereof
WO2021245671A1 (en) * 2020-06-03 2021-12-09 Epm (Ip), Inc. Cannabidiolic acid (cbda) derivatives and uses thereof

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6410596B1 (en) * 2000-08-16 2002-06-25 Insmed Incorporated Compositions containing hypoglycemically active stillbenoids
US6541522B2 (en) * 2000-08-16 2003-04-01 Insmed Incorporated Methods of using compositions containing hypotriglyceridemically active stilbenoids
NL2006621C2 (en) * 2011-04-18 2012-10-22 Fytagoras B V New medical use for acidic cannabinoids.
CN105030750B (zh) 2011-12-23 2018-08-28 中国医学科学院医药生物技术研究所 一组木豆素结构类似化合物在抗丙肝病毒和抗艾滋病毒的应用
JP2021525268A (ja) * 2018-05-31 2021-09-24 ソシエテ・デ・プロデュイ・ネスレ・エス・アー Ａｍｐｋ直接活性化剤化合物
US12403114B2 (en) * 2019-03-12 2025-09-02 Epm (Ip), Inc. Cannabinoid acid ester compositions and uses thereof
EP4013397A1 (de) * 2019-08-13 2022-06-22 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd Phytocannabinoide zur vorbeugung oder behandlung von nicht-alkoholischer fettlebererkrankung, dyslipidämie und typ-2-diabetes

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021245672A1 (en) * 2020-06-03 2021-12-09 Epm (Ip), Inc. Cannabigerolic acid (cbga) derivatives and uses thereof
WO2021245671A1 (en) * 2020-06-03 2021-12-09 Epm (Ip), Inc. Cannabidiolic acid (cbda) derivatives and uses thereof

Also Published As

Publication number Publication date
EP4240342A1 (de) 2023-09-13
JP7833458B2 (ja) 2026-03-19
US20230414638A1 (en) 2023-12-28
CN116761791A (zh) 2023-09-15
WO2022096423A1 (en) 2022-05-12
AU2021375455A1 (en) 2023-04-20
JP2023547641A (ja) 2023-11-13
CA3192827A1 (en) 2022-05-12

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